May in Capri

Every May, just before the island shakes off its spring quiet and slips into high-summer bustle, we sail back to Capri and it feels like opening a well-loved novel to a fresh chapter. The wisteria is still lingering on the villa walls, the jasmine is just beginning to perfume the narrow lanes, and the light has that soft, pearly glow that flatters every limestone cliff. Over the years we’ve come to treat this shoulder-season interlude as an annual tune-up for the spirit: mornings steeped in espresso and sea-spray, afternoons wandering stone stairways in search of the next perfect view, evenings that unravel slowly over plates of pasta and the pop of a chilled Falanghina. Below are the addresses we reached for again and again on this trip—each one stamped with a memory and a little dose of May-in-Capri magic. (Plus, everything I wore on the trip!)

Our home base this year was the quaint Sina Capri, which sits next to the Grand Hotel Quisissana, but offers the same seaviews for a fraction of the price. We booked a Seaview Premium Junior Suite and it was wonderfully spacious with a long balcony for sipping our morning espresso with views of the water. Think lemon-scented terraces, a petite pool edged with bougainvillea, and crisp white-on-white rooms that keep the focus on the sapphire water beyond the balcony. The staff greet you by name after day one, and the breakfast spread was perfect for early morning meals with a baby.

La Grottelle
Half-taverna, half-cave, all romance. Reached via the quiet Pizzolungo path, La Grottelle serves unfussy, grandfather-approved dishes. We love coming here for a long lunch. Be sure to reserve a table at the edge for sweeping views of the water (though we prefer tables further back when traveling with a baby.) After your meal, walk down to the Arco Naturalle for a stunning view.

J.K. Place Capri

Slip through the discreet gates of J.K. Place and you’re in a film set: blue and white deck chairs, white-beam ceilings, and a teak-decked terrace cantilevered over Marina Grande. We cuddled up in the oversize couches for aperitivo, then as dusk fell on Mount Vesuvius across the bay, we traded cushions for a linen-draped table just a few steps away. Our table looked out on the mainland coastline shimmering like a string of pearls. It’s Capri elegance distilled: relaxed and impeccable. I'd love to stay here on a future trip!

The terrace of the Grand Hotel Quisisana is Capri’s living postcard, and its Negroni game is unmatched. Order one and an entire flotilla of snacks will land on your table: focaccia, olives, smoked salmon, caprese. We stopped by three evenings in a row, watching the carousel of island fashion saunter past our table while the setting sun made the hotel’s ochre facade glow. Tip: it's a great spot even if it's raining - snag a table on the far left side of the terrace under the awning, where they often have live music performing even if there's a drizzle. They don't serve a lot of larger dishes on the terrace, but their ham and cheese sandwich is delicious.

Panorama
A short descent from the Piazzetta rewards you with a modern terrace and pizza pies that rival Naples. We've been coming here on our first night in Capri for several years and the staff remembers us. (Perhaps because it's on the more elegant side and no one else brings a baby!) On clear evenings the roof is retracted, and you dine between a row of lemon trees and the expanse over Marina Grande, but if it's raining they have you covered and it's still a special spot.

One level down from the bus station—and sharing that sweeping Marina Grande vista with Panorama—Verginiello is know for their generous plates without the sky-high Capri prices. Locals mix with savvy travelers over paper-thin pizzas (try the “Diavola” for a spicy kick), grilled calamari (the best we had on Capri), and carafes of chilled Falanghina. The service is warm, and tables turn quickly; arrive early or be prepared to queue.

Tucked into the rocks just below Via Krupp, Torre Saracena feels like a secret fortification turned rustic seafood outpost. We came with our Milanese friends and settled into a large table right on the water—waves lapping the stone steps. The must-order dish here is the famous pasta with peas and almonds - sounds a bit weird but trust me! Go for a late lunch, then melt into a pair of loungers until the cliffs blush pink, and you’ll understand why locals treat it as a favorite hideaway. (The beach is a gentle slope which is great for kids but very rocky. I definitely recommend bringing water shoes--which we didn't have.)

La Fontelina Beach Club
Iconic blue-and-white umbrellas, platforms scattered amongst the rocks, and views that frame the Faraglioni like a postcard—Fontelina needs no introduction. Reserve your lunch table and loungers weeks ahead, skip breakfast, and pace yourself: indulge in simple, fresh dishes like burrata and tomatoes, spaghetti, and affogato the experience will ruin you for lunch anywhere else. Afterwards take your unfinished bottle of wine down to your spot on the rocks, and jump in for a swim. You can reach the beach club by a long winding staircase or complementary boat transfer from Marina Piccola. Fontelina welcomes children, but it isn't the easiest place for small children to swim.